Sodium hydride → (+)-2-{4-(1-Hexyloxyethyl)phenyl}-5-decyloxypyrimidine

HRID 274177

Reaction equation

HRID 274177 reaction equation
[OH:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:12][N:11]=2)=[CH:6][CH:5]=1)[CH3:3].[H-].[Na+].[C:29]1(C)[CH:34]=[CH:33][C:32](S(OCCCCCC)(=O)=O)=[CH:31][CH:30]=1>O>[CH2:33]([O:1][CH:2]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:12][N:11]=2)=[CH:8][CH:9]=1)[CH3:3])[CH2:34][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 220448Hexyl p-ToluenesulfonateHCID 214682802-(4-(1-Hydroxyethyl)phenyl)-5-decyloxypyrimidine

Product 1

HCID 54404658(+)-2-{4-(1-Hexyloxyethyl)phenyl}-5-decyloxypyrimidineYield 82.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

Into 20 ml of anhydrous dlmethylformamide were dissolved 1.78 g (5 millimole) of the (+)-2-{4-(1-hydroxyethyl)phenyl}-5-decyloxypyrimidine obtained in Preparation Example [starting material compound (VI)] 70, and then 0.24 g (6 millimole) of 60% sodium hydride was added thereto, followed by stirring at 40° C. for 1 hour. Subsequently, 1.79 g (7 millimole) of hexyl p-toluenesulfonate were added thereto, to subject to reaction at the same temperature for 2 hours. After completion of the reaction, the reaction mixture was poured into 200 ml of water, extracted with 200 ml of toluene, followed by separation thereof, and the organic phase was washed with water sufficiently, followed by drying over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography (eluent; toluene: ethyl acetate) to obtain 1.81 g (yield: 82%) of (+)-2-{4-(1-hexyloxyethyl)phenyl}-5-decyloxypyrimidine.

Workup

  1. customto subject to reaction at the same temperature for 2 hours
  2. customAfter completion of the reaction
  3. extractionextracted with 200 ml of toluene
  4. customfollowed by separation
  5. washthe organic phase was washed with water sufficiently
  6. dry with materialby drying over anhydrous magnesium sulfate
  7. distillationAfter the solvent was distilled off under reduced pressure
  8. customthe resulting residue was purified by silica gel column chromatography (eluent; toluene: ethyl acetate)

Sources & evidence

ORD record
ord-b893edb234c34782b8663ea06395fd3f
Source dataset
uspto-grants-1995_02
Patent number
US05389293

Linked notes

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